Water → HCID 66625866, compound

HRID 1629669Notes

Reaction equation

HRID 1629669 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([OH:13])[CH2:7][CH:8]([CH3:12])[NH:9]2)=[CH:4][CH:3]=1.[C:14](Cl)(=[O:16])[CH3:15].[OH2:18].N1[CH:24]=[CH:23]C=CC=1>ClCCl>[C:14]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)[CH:6]([O:13][C:23](=[O:18])[CH3:24])[CH2:7][CH:8]1[CH3:12])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 66625696HCID 66625696, compound

Product 1

HCID 66625866HCID 66625866, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Step 2) 860 mg of 7-fluoro-4-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline as a brown oily substance was dissolved in 0.5 mL of pyridine and 10 mL of dichloromethane, and 16 mg of acetyl chloride was added to the solution under ice cooling. The mixture was stirred for 1.5 hours. After completion of the reaction, water was added to the reaction liquid, and the mixture was extracted with chloroform. Subsequently, the organic layer was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (ethyl acetate:hexane=1:2), and thus 1.9 g (100%) of 1-acetyl-7-fluoro-4-acetoxy-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as an oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionthe mixture was extracted with chloroform
  3. concentrationwas concentrated under reduced pressure
  4. customThe resulting residue was purified

Sources & evidence

ORD record
ord-118c1bf0e5164543aa863d22b42ed36a
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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